Cationic benzoxazine (co)polymers

Abstract

Cationic benzoxazine (co)polymers wherein at least 5% of all nitrogen atoms are in the form of quaternary nitrogen atoms, and to a method for producing said polymers. The invention also relates to a washing and cleaning agent, a textile treatment agent or a cosmetic agent containing at least one cationic benzoxazine (co)polymer according to the invention.

1. Cationic benzoxazine (co)polymer, wherein at least 5% of all the nitrogen atoms, relative to the total number of all the nitrogen atoms in the cationic benzoxazine (co)polymer, are present in the form of permanently quaternary nitrogen atoms,
 wherein the cationic benzoxazine (co)polymer is produced by 
 providing at least one polymerizable benzoxazine compound; 
 producing a non-cationic benzoxazine (co)polymer by polymerizing the at least one polymerizable benzoxazine compound under suitable polymerization conditions, 
 wherein less than 1% of nitrogen atoms of the non-cationic benzoxazine (co)polymer, relative to the total number of nitrogen atoms in the non-cationic benzoxazine (co)polymer, are present in the form of permanently quaternary nitrogen atoms, and 
 reacting the non-cationic benzoxazine (co)polymer with at least one alkylating agent in an amount wherein at least 5% of all nitrogen atoms, relative to the total number of nitrogen atoms in the non-cationic benzoxazine (co)polymer, are converted into permanently quaternary nitrogen atoms. 
 
     
     
       2. Cationic benzoxazine (co)polymer according to  claim 1 , wherein the polymerizable benzoxazine compound chosen from compounds of general formula (I) and compounds of general formula (II), 
       
         
           
           
               
               
           
         
         wherein 
         q is an integer from 1 to 4; 
         n is a number from 2 to 20,000; 
         R in each repeat unit is mutually independently chosen from hydrogen or linear or branched, optionally substituted alkyl groups having 1 to 8 carbon atoms; 
         Z is chosen from hydrogen (where q=1), alkyl (where q=1), alkylene (where q=2 to 4), carbonyl (where q=2), oxygen (where q=2), sulfur (where q=2), sulfoxide (where q=2), sulfone (where q=2) and a direct, covalent bond (where q=2); 
         R 1  is a covalent bond or is a divalent linking group having 1 to 100 carbon atoms; 
         R 2  is chosen from hydrogen, halogen, alkyl and alkenyl or R 2  is a divalent residue which makes a corresponding naphthoxazine structure from the benzoxazine structure; 
         Y is chosen from linear or branched, optionally substituted alkyl groups having 1 to 15 carbon atoms, cycloaliphatic residues optionally containing one or more heteroatoms, aryl residues optionally containing one or more heteroatoms and *—(C═O)R 3 , 
         wherein R 3  is chosen from linear or branched, optionally substituted alkyl groups with 1 to 15 carbon atoms and X—R 4 , wherein X is chosen from S, O, and NH and R 4  is chosen from linear or branched, optionally substituted alkyl groups with 1 to 15 carbon atoms; 
         c is an integer from 1 to 4; 
         B is chosen from hydrogen (where c=1), alkyl (where c=1), alkylene (where c=2 to 4), carbonyl (where c=2), oxygen (where c=2), sulfur (where c=2), sulfoxide (where c=2), sulfone (where c=2) and a direct, covalent bond (where c=2); 
         A is a hydroxyl group or a nitrogenous heterocycle; 
         R 5  is chosen from hydrogen, halogen, alkyl and alkenyl or R 5  is a divalent residue which makes a corresponding naphthoxazine structure from the benzoxazine structure; and 
         R 6  is a covalent bond or is a divalent linking group having 1 to 100 carbon atoms. 
       
     
     
       3. Cationic benzoxazine (co)polymer according to  claim 2 , wherein the polymerizable benzoxazine compound is chosen from compounds of general formula (III), 
       
         
           
           
               
               
           
         
       
       wherein x is a number from 0 to 1000 and y is a number from 0 to 1000, with the proviso that x+y≧2, and Z, R 2 , Y and q are as defined in  claim 2 . 
     
     
       4. Cationic benzoxazine (co)polymer according to  claim 2 , wherein the polymerizable benzoxazine compound is chosen from compounds of general formula (IV) and compounds of general formula (V), 
       
         
           
           
               
               
           
         
       
       wherein R 7  and R 8  are mutually independently chosen from hydrogen, halogen, linear or branched, optionally substituted alkyl groups, alkenyl groups and aryl groups; and c, B, R 5  and R 6  are as defined in  claim 2 . 
     
     
       5. Cationic benzoxazine (co)polymer according to  claim 1 , wherein the at least one alkylating agent is chosen from alkyl halides, dialkyl sulfates, dialkyl carbonates and alkylene oxides. 
     
     
       6. Cationic benzoxazine (co)polymer according to  claim 1 , wherein the cationic benzoxazine (co)polymer has a molecular weight of 500 to 100,000 g/mol. 
     
     
       7. Washing and cleaning agent or textile treatment agent comprising at least one cationic benzoxazine (co)polymer according to  claim 1 . 
     
     
       8. Cosmetic agent comprising in a cosmetically acceptable carrier at least one cationic benzoxazine (co)polymer according to  claim 1 . 
     
     
       9. Method for treating a surface comprising the steps of:
 providing at least one cationic benzoxazine (co)polymer according to  claim 1  in an applicable dosage form, and 
 treating at least one surface with the cationic benzoxazine (co)polymer provided. 
 
     
     
       10. Method for treating a surface according to  claim 9 , wherein the surface is chosen from carbon fibers, hard surfaces, textile surfaces and keratin fibers. 
     
     
       11. Method for producing a cationic benzoxazine (co)polymer having at least 5% of all nitrogen atoms, relative to the total number of nitrogen atoms in the cationic benzoxazine (co)polymer, present in the form of permanently quaternary nitrogen atoms, comprising the steps:
 providing at least one polymerizable benzoxazine compound; 
 producing a non-cationic benzoxazine (co)polymer by polymerizing the at least one polymerizable benzoxazine compound under suitable polymerization conditions, 
 wherein less than 1% of nitrogen atoms of the non-cationic benzoxazine (co)polymer, relative to the total number of nitrogen atoms in the non-cationic benzoxazine (co)polymer, are present in the form of permanently quaternary nitrogen atoms, and 
 reacting the non-cationic benzoxazine (co)polymer with at least one alkylating agent in an amount wherein at least 5% of all nitrogen atoms, relative to the total number of nitrogen atoms in the non-cationic benzoxazine (co)polymer, are converted into permanently quaternary nitrogen atoms. 
 
     
     
       12. Coupling agent, sizing agent, hair conditioning agent and/or hair shaping agent comprising a cationic benzoxazine (co)polymer according to  claim 1 . 
     
     
       13. Method of coating surfaces comprising applying a composition containing a cationic benzoxazine (co)polymer according to  claim 1  to a surface to be coated. 
     
     
       14. Method of coating surfaces according to  claim 13  wherein the composition forms a coating when applied to the surface and the coating is an antibacterial coating. 
     
     
       15. Method of improving soil detachment from and/or reducing susceptibility to soil redeposition onto textiles or hard surfaces comprising applying an agent containing a cationic benzoxazine (co)polymer according to  claim 1  onto the textile or hard surface.